Sunday, May 28, 2017

Crossdressing Caption - An Irresistible Deal


8 comments:

  1. Sammy definitely lost that bet. I wonder how many dates he has set up after that day out?

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  2. Hmm, I suspect somebody has 3 months as a sexy little sister ahead of them!

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    1. Oh, I think it's going to go on for a LOT longer than three months. I'm guessing he's never going back, no matter what he wants.

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  3. Omg this outfit is INCREDIBLE! Great idea too! Is there more to this original image?

    Will the sister introduce a new term? "Okay, you won, but now you have to choose 1 of the guys who hit on you to go out on a date with! No ifs ands or buts! If you don't choose, I'll choose FOR you. Or else..."

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    1. I couldn't find any other photos from the shoot this came from, so I guess it's a one-off picture. I looked, too, because I originally wanted a view from the front. And I'm sure she'll find a few more bets along the way. My guess is that he'll never really be a boy again.

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    2. Ahh searched in google images, couldn't even find the source so yeah looks like it's just a one off ahh

      Hmm, maybe if he really behaves, she'll let him go "back to boy clothes"...that make him look like a total fairy twink. That's about as boyish as he'll ever be allowed to dress again! I bet after a month as a little sister, even if he's allowed to dress himself again, he'll just end up dressing up a girly-boy anyways without even realizing. Older sister will teach her well.

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